Insight of solvent effect on CeO2 catalyzed oxidation of styrene with tert-butyl hydroperoxide: A combined experimental and theoretical approach

Halder, Jyotirmoy; Roy, Tarun Kumar; Satpati, Sayon; Ghosal, Subhas; Mukherjee, D. K.; Reddy, Benjaram M.

doi:10.1016/j.catcom.2022.106413

Cited by 5 publications

(3 citation statements)

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“…The reasons why solvents cause the deterioration of catalytic performance may be that solvent molecules may directly or indirectly influence the energetics of adsorbate, transition state, and intermediate through interactions at a solid−liquid interface. 54,55 Analysis of styrene contents and product distributions during the tandem reaction catalyzed by IL-Au@UiO-66-NH 2 /CMC and carried out under the optimized conditions described above, depicted in Figure 4A, shows that the conversion of styrene and selectivity for SC steadily increases as the reaction time increases from 4 to 28 h and then remains unchanged after reaching a maximum conversion of 90.5% and selectivity of 80.5% within 24 h. During the process, amounts of the main byproduct benzaldehyde and intermediate styrene oxide (SO) remain low. To evaluate the features of the multicomponent and hierarchical catalyst IL-Au@UiO-66-NH 2 /CMC that influence its superior activity, performances of various related materials having different compositions and structures were tested (Figure 4B).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Inspection of catalytic performances of IL-Au@UiO-66-NH 2 /CMC containing varied Au amounts (Table ) revealed that IL-Au 0.21 wt % @UiO-66-NH 2 /CMC (60 mg, hereafter denoted as IL-Au@UiO-66-NH 2 /CMC) displays the best performance (90.5% conversion of styrene and 80.5% selectivity for SC formation) for the solvent-free reaction of styrene (2 mmol), TBHP (255 mg), and TBAB (62.5 mg) using 0.1 MPa CO 2 at 80 °C for 24 h. In addition, we found that solvents retard the efficiency of this process (Table entries 5–7) with high polarity DMF having the lowest retardation effect (89.4% styrene conversion vs 90.5% conversion under solvent-free conditions) (Table entry 3). The reasons why solvents cause the deterioration of catalytic performance may be that solvent molecules may directly or indirectly influence the energetics of adsorbate, transition state, and intermediate through interactions at a solid–liquid interface. , …”

Section: Resultsmentioning

confidence: 99%

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A Hierarchical Metal–Organic Framework Composite Aerogel Catalyst Containing Integrated Acid, Base, and Metal Sites for the One-Pot Catalytic Synthesis of Cyclic Carbonates

Zhao,

Chang,

et al. 2024

ACS Appl. Mater. Interfaces

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Catalysis has played a decisive role in the development of unique chemical reactions to produce important chemicals. However, conventional stepwise synthetic routes that rely on individual catalysts to promote each step often suffer from ponderous processes for the isolation of intermediates that result in massive material losses and large economic expenditures. In addition, traditional powder forms of these catalysts suffer from poor processability and recoverability. Herein, we designed and prepared a hierarchical metal−organic framework (MOF) composite monolithic catalyst IL-Au@UiO-66-NH 2 /CMC that contains integrated acid (Zr 4+ ), base (ionic liquid (IL)), and metal sites (Au nanoparticles (NPs)) to promote the one-pot preparation of cyclic carbonates from styrene derivatives and CO 2 . Highly dispersed Au NPs, IL 1-aminoethyl-3-methylimidazolium bromide ([C 2 NH 2 MIM] [Br]), and MOF-positioned Lewis acid sites within this composite aerogel are separately responsible for catalyzing selective epoxidation of the styrene derivatives and the subsequent cycloaddition reaction of CO 2 with intermediate styrene oxides. Importantly, inclusion of the imidazolium-based IL effectively modulates the size and chemical microenvironment of the Au NPs via electrostatic protection, leading to catalyst stability and its selective oxidation of styrene. Benefiting from the rapid mass transfer and high exposure of active sites within the pore-rich hierarchical nanostructure, IL-Au@UiO-66-NH 2 /CMC promotes high conversion (90.5%) of the styrene and selectivity (80.5%) for styrene carbonate (SC) formation in the one-pot process, a performance level that far exceeds those of related catalysts containing only Au NPs or IL (the selectivity of SC < 42%). Furthermore, the composite aerogel catalyst can be readily separated and recycled at least five times without a remarkable loss of activity and selectivity. The controllable integration of various active components in the hierarchical MOF composite aerogel herein should serve as the foundation for the design of multifunctional monolithic catalysts for other valuable tandem processes.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

A Hierarchical Metal–Organic Framework Composite Aerogel Catalyst Containing Integrated Acid, Base, and Metal Sites for the One-Pot Catalytic Synthesis of Cyclic Carbonates

Zhao,

Chang,

et al. 2024

ACS Appl. Mater. Interfaces

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“…Use of CHP as oxidizing agent for styrene oxidation has been delineated to have advantage of producing alpha cumyl alcohol (ACA) as value-added co-product upon breakage of peroxy bond. 6,7,25 Metal oxides have shown excellent catalytic activities for homologous reactions like styrene oxidation using other oxidants like hydrogen peroxide, 27 tert-butyl hydroperoxide, 28 and molecular oxygen. 29 Based on observed experimental results and published…”

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confidence: 99%

One‐pot synthesis of phenylacetaldehyde from styrene via metal oxide catalysed oxidation in presence of cumene hydroperoxide

Das

2024

Flavour & Fragrance J

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Phenylacetaldehyde (PhA) is an aromatic aldehyde which has a hyacinth‐like floral, sweet and green‐leafy odour. PhA is used as a perfumery chemical and a rate‐controlling additive in cosmeceutical and polymer industries, respectively. The conventional process of PhA manufacturing in industries involve hazardous and costly feedstock and often lead to generation of substantial amount of waste. Moreover, usage of stoichiometric reagents often makes the processes economically impractical. This article illustrates the possibility of production of PhA from low‐cost feedstock styrene through a single‐step, one‐pot method wherein various metal oxides have been utilized as catalysts for styrene oxidation under the influence of cumene hydroperoxide (CHP). Ag2O is found to be the highest PhA‐yielding catalyst and a promising candidate for scaling up for its considerably good reusability up to 6 consecutive uses. A maximum of ~45% PhA selectivity has been observed at ~60% styrene conversion. Interestingly, this process does not require any alkaline/acid wash and hence does not produce any organic/inorganic liquid effluent stream. Furthermore, all the major byproducts found, that is styrene oxide, benzaldehyde and acetophenone, are themselves considered as valorized styrene derivatives. Overall, the metal oxide catalysed styrene oxidation has potential to take over the conventional industrial process(es) for sustainable selective production of PhA Along with a plausible mechanism of styrene oxidation over Ag2O, a conceptualized reaction–separation framework has been reported for intensified production of PhA from CHP‐based styrene oxidation.

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Cobalt Supported on Ce-MOF-Derived CeO2 as a Catalyst for the Efficient Epoxidation of Styrene Under Aerobic Conditions

Sun,

Wang,

Zhao

et al. 2024

Catal Lett

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Insight of solvent effect on CeO2 catalyzed oxidation of styrene with tert-butyl hydroperoxide: A combined experimental and theoretical approach

Cited by 5 publications

References 24 publications

A Hierarchical Metal–Organic Framework Composite Aerogel Catalyst Containing Integrated Acid, Base, and Metal Sites for the One-Pot Catalytic Synthesis of Cyclic Carbonates

A Hierarchical Metal–Organic Framework Composite Aerogel Catalyst Containing Integrated Acid, Base, and Metal Sites for the One-Pot Catalytic Synthesis of Cyclic Carbonates

One‐pot synthesis of phenylacetaldehyde from styrene via metal oxide catalysed oxidation in presence of cumene hydroperoxide

Cobalt Supported on Ce-MOF-Derived CeO2 as a Catalyst for the Efficient Epoxidation of Styrene Under Aerobic Conditions

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